Dimethyl Sulfoxide → HCID 88117181, compound

HRID 1860511Notes

Reaction equation

HRID 1860511 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:13]=[C:14]([C@H:18]2[C@H:22]([CH2:23][OH:24])[CH2:21][N:20]([CH2:25][C:26]3([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:19]2)[CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]1[CH:13]=[C:14]([C@H:18]2[C@H:22]([CH:23]=[O:24])[CH2:21][N:20]([CH2:25][C:26]3([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[CH2:19]2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22977894HCID 22977894, compound

Product 1

HCID 88117181HCID 88117181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (0.6 mL, 7 mmol) in 35 mL CH2Cl2 was cooled to −78° C. and DMSO (1 mL, 14.1 mmol) was added dropwise. After stirring for 20 min a solution of Benzyl 1-{[(3R,4S)-3-(3-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-1-yl]methyl}cyclohexane carboxylate (2.5 g, 5.88 mmol, from Step C) in 35 mL CH2Cl2 was added. The mixture was stirred for 20 min more then triethylamine (4 mL, 29.5 mmol) was added. The cooling bath was removed and the mixture was stirred for 4h. 100 mL CH2Cl2 was added and the mixture was washed with 1 M NaOH then water and sat'd sodium chloride. The organic layer was dried over magnesium sulfate and concentrated. Flash chromatography (90 g silica, 5/1 hexane/EtOAc) gave the desired aldehyde. 1H NMR (500 MHz, CDCl3) δ1.25-1.43 (m, 6H), 1.58-1.63 (m, 4H), 2.15-2.19 (m, 2H), 2.62-2.73 (m, 2H), 2.83-2.87 (m, 1H), 2.92-3.01 (m, 2H), 3.44-3.51 (m, 1H), 5.11-5.21 (dd, 2H), 6.9-6.97 (m, 1H), 6.98-7.13 (m, 2H), 7.23-7.4 (m, 6H), 9.6 (s, 1H).

Workup

  1. additionwas added
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred for 4h
  4. addition100 mL CH2Cl2 was added
  5. washthe mixture was washed with 1 M NaOH
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e54d410af364faca2af1d6c47c4a405
Source dataset
uspto-grants-2003_03
Patent number
US06531484B2

Reaction notes

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